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Zvi comments on (Virtual) Employment Open Thread - Less Wrong
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I think I could probably get that to happen if I tried for a few months to a year. What's the next step? Move in together and not pay any of the rent? I have a girl in Berkeley who I could move in with for free now, but she likes me a lot more than I like her, and I think I'd feel way too guilty about that.
(I'm not really that interested in getting money; I volunteer/intern for SIAI which allows me to live comfortably. But I empathize with the counterfactual me that didn't have that option, or the possible future where my skills are no longer useful to SIAI. Therefore, more knowledge is good.)
Unless you are deceiving her in some way, my suggestion is to try and find a way to not feel guilty about this. That doesn't mean do it, since it might still not be worth it, but you have nothing to feel guilty about.
I have been in a situation. I have liked a girl a lot more than she liked me, known this and asked her to move in with me (rent free) anyway. I had the ability to do so, and I valued our time together and the chance to try for something more. It didn't work out, but I don't resent her or regret it. Given another chance I'd do it again.